WO1997012586A1 - Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer - Google Patents
Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer Download PDFInfo
- Publication number
- WO1997012586A1 WO1997012586A1 PCT/FR1996/001436 FR9601436W WO9712586A1 WO 1997012586 A1 WO1997012586 A1 WO 1997012586A1 FR 9601436 W FR9601436 W FR 9601436W WO 9712586 A1 WO9712586 A1 WO 9712586A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- meth
- acrylate
- monomers
- silicone
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- -1 polysiloxane backbone Polymers 0.000 title claims abstract description 56
- 229920000642 polymer Polymers 0.000 title claims abstract description 33
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 29
- 229920005573 silicon-containing polymer Polymers 0.000 title claims description 41
- 230000000699 topical effect Effects 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 239000002537 cosmetic Substances 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 29
- 150000003254 radicals Chemical class 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 239000002562 thickening agent Substances 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000006260 foam Substances 0.000 claims description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 102000011782 Keratins Human genes 0.000 claims description 5
- 108010076876 Keratins Proteins 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 230000000475 sunscreen effect Effects 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 238000002845 discoloration Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000006200 vaporizer Substances 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 1
- 239000008158 vegetable oil Substances 0.000 claims 1
- 230000003750 conditioning effect Effects 0.000 abstract description 2
- 229920000578 graft copolymer Polymers 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract 1
- 229920002125 Sokalan® Polymers 0.000 description 16
- 229920001897 terpolymer Polymers 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003745 detangling effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- UKXDHEBARGMWMO-ARJAWSKDSA-N (z)-4-(2-methylpropoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)COC(=O)\C=C/C(O)=O UKXDHEBARGMWMO-ARJAWSKDSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QPEVJKSFYHPLBL-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)OC=C.C(C(=C)C)(=O)O Chemical compound C(CCCCCCCCCCCCCCCCC)OC=C.C(C(=C)C)(=O)O QPEVJKSFYHPLBL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 description 1
- GADGVXXJJXQRSA-UHFFFAOYSA-N ethenyl 8-methylnonanoate Chemical compound CC(C)CCCCCCC(=O)OC=C GADGVXXJJXQRSA-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/899—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
Definitions
- the present invention relates to a cosmetic or dermatological composition for the treatment of keratin materials, in particular human hair, comprising at least one grafted silicone polymer, with a polysiloxane skeleton grafted with non-silicone organic monomers and at least one amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit.
- Polymers of the grafted silicone polymer type with a polysiloxane backbone grafted with non-silicone organic monomers are known in the prior art for their styling properties. They are particularly advantageous in hair cosmetics because they provide hold to the hair. Their cosmetic properties after application to the hair are nevertheless insufficient. It is found that the hair has, after application of these polymers, a rough and crunchy feel resulting from a discontinuous distribution of the polymer along the fibers of the hair.
- an amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit, as thickening agent in hair compositions containing a polymer with a polysiloxane backbone grafted with non-silicone organic monomers , not only made it possible to increase the viscosity of the medium of these compositions in an increased manner but also to improve, on application, the deposition of the silicone polymer grafted along the keratin fibers and to improve their cosmetic properties, in particular at the level of the touch as well as at the disentangling, while retaining the styling properties of the grafted silicone polymer.
- composition according to the invention is therefore essentially characterized in that it contains in a cosmetically or dermatologically acceptable medium at least one grafted silicone polymer, with a polysiloxane backbone grafted with non-silicone organic monomers and at least one amphiphilic polymer comprising at at least one fatty chain and at least one hydrophilic unit.
- sicone polymer is intended to denote, in accordance with general acceptance, all organosilicon polymers or oligomers with linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and / or polycondensation of silanes suitably functionalized, and essentially consisting of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bond ⁇ Si-O-Si ⁇ ), optionally substituted hydrocarbon radicals being directly linked via a carbon atom on said silicon atoms.
- hydrocarbon radicals are alkyl radicals, especially C 1 -C 10 and in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl, and alkenyl radicals and in particular vinyl; other types of radicals capable of being linked either directly or via a hydrocarbon radical to the siloxane chain are in particular hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, poiyoxyalkylenated (or polyether) radicals and in particular polyoxyethylene and / or polyoxypropylene radicals, hydroxyl or hydroxyalkyl radicals, substituted or unsubstituted amino groups, amide groups, acyloxy or acyloxyalkyl radicals, hydroxyalkylamino radicals or aminoalkyls, quaternary ammonium groups, amphoteric or betainic groups, anionic groups such as carboxylates, thioglycolates, sulfos,
- the silicone polymer (s) which must be used are those which comprise a main silicone chain (or polysiioxane ( ⁇ Si-0-) n ) on which is grafted, inside said chain as well as 'optionally at at least one of its ends, at least one organic group not comprising silicone.
- These silicone polymers can be existing commercial products, or can also be obtained by any means known to those skilled in the art, in particular by reaction between (i) a starting silicone correctly functionalized on one or more of these silicon atoms.
- silicone polymers suitable for the implementation of the present invention are described in particular in patent applications EP-A-0582152, WO93 / 23009 and WO 95/03776, the teachings of which are fully included in this description by way of non-limiting references.
- the silicone polymer used comprises the result of radical copolymerization between on the one hand at least one non-silicone anionic organic monomer having ethylenic unsaturation and / or one hydrophobic organic monomer non-silicone having ethylenic unsaturation and on the other hand a silicone having in its chain at least one functional group capable of reacting on said ethylenic unsaturations of said non-silicone monomers by forming a covalent bond, in particular thio-functional groups.
- said anionic ethylenically unsaturated monomers are preferably chosen, alone or as a mixture, from unsaturated, linear or branched carboxylic acids, optionally partially or completely neutralized in the form of a salt, this or these unsaturated carboxylic acids may more particularly be acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid.
- Suitable salts are especially the alkali, alkaline earth and ammonium salts.
- the organic group with an anionic character which comprises the result of the (homo) radical polymerization of at least one anionic monomer of acid type unsaturated carboxylic acid can be, after reaction, post-neutralized with a base (soda, ammonia, etc.) to bring it in the form of a salt
- the hydrophobic ethylenically unsaturated monomers are preferably chosen, alone or as a mixture, from acrylic acid alkanol esters and / or methacrylic acid esters from alkanols.
- the alkanols are preferably in C r C ⁇ a and more particularly in C r C 12
- the preferred monomers are chosen from the group consisting of isooctyl (meth) acrylate, isononyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, isopentyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, methyl (meth) acrylate, tert-butyl (meth) acrylate, t ⁇ decyl (meth) acrylate, stearyl (meth) acrylate or mixtures thereof
- a family of silicone polymers grafted particularly well to the implementation of the present invention consists of silicone polymers comprising in their structure the unit of formula (I) below.
- G 1 f represent hydrogen or a C 1 -C 10 alkyl radical or else a phenyl radical
- the G 2 radicals, identical or different represent a C ⁇ -C 10 alkylene group
- G 3 represents a polymer residue resulting from the (homo) polymé ⁇ sat ⁇ on of at least one anionic monomer with ethylenic unsaturation
- G 4 represents a polymer residue resulting from the (homo) polymerization of at least one hydrophobic ethylenically unsaturated monomer
- m and n are 0 or 1
- a is an integer ranging from 0 to 50
- b is an integer which can be between 10 and 350
- c is an integer ranging from 0 and 50, provided that one of the parameters a and c is different from 0
- the motif of formula (I) above has at least one, and even more preferably all, of the following characteristics
- radicals G- denote an alkyl radical, preferably the methyl radical
- radicals G 2 represent a divalent C 1 -C 3 radical, preferably a propylene radical;
- - G 3 represents a polymer radical resulting from the (homo) polyménsat ⁇ on of at least one monomer of the carboxylic acid type with ethylenic unsaturation, preferably acrylic acid and / or methacrylic acid;
- G 4 represents a polymeric radical resulting from the (homo) polymerization of at least one monomer of the (meth) acrylate (C 1 -C 1 0) type, preferably isobutyl (meth) acrylate or methyl.
- silicone polymers corresponding to formula (I) are in particular polydimethylsiloxanes (PDMS) onto which are grafted, via a thiopropylene-type connecting link, mixed polymer units of the poly (meth) acrylic acid type. and of the poly (meth) acrylate type.
- PDMS polydimethylsiloxanes
- silicone polymers corresponding to formula (I) are in particular polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting link, polymeric units of the poly (meth) acrylate type. isobutyl
- the number-average molecular mass of the silicone polymers of the invention varies from approximately 10,000 to 1,000,000, and even more preferably from approximately 10,000 to 100,000
- the grafted silicone polymer is preferably used in an amount ranging from 0.01 to 20% by weight of the total weight of the composition. More preferably, this amount varies from 0.1 to 15% by weight and even more preferably from 0.5 to 10% by weight
- amphiphilic polymers comprising at least one fatty chain and at least one hydrophilic unit, used according to the invention are preferably chosen from the group consisting of:
- holosides modified by groups comprising at least one fatty chain
- celluloses or their derivatives modified by groups comprising at least one fatty chain such as alkyl, arylalkyl, alkylaryl groups or their mixtures where the alkyl groups are C 8 -C 22 ;
- nonionic alkylhydroxyethylcelluloses such as the products NATROSOL PLUS GRADE 330 CS and POLYSURF 67 (C 16 alkyl) sold by the company AQUALON;
- quaternized (cationic) alkylhydroxyethylcelluloses such as the products QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18-
- non-ionic nonoxynylhydroxyethyicelluloses such as the product AMERCELL HM-1500 sold by the company AMERCHOL;
- non-ionic alkylcelluloses such as the product BERMOCOLL EHM 100 sold by the company BEROL NOBEL;
- C ⁇ 2 -C 18 polyalcohols (C ⁇ 2 -C 18 ) saccharides
- EMULSAN D-galactosamine / aminouronic acid mixture
- BIOSAN LPS-50 sold by the company PETROFERM
- N-octadecylvinylether / maleic anhydride copolymers such as the product GANTREZ AN-8194 sold by the company ISP; - the vinyl acetate / isobutyl monomaleate / vinyl neodecanoate terpolymers such as the products ACV-4033 and 9649-147 sold by ISP, the product MEYPRO-FIX 509 sold by MEYHALL and the products DENSODRIN BA and LIPODERM LIQUOR FP sold by BASF;
- polyurethanes and their derivatives comprising groups containing at least one fatty chain
- RHEOLATE 205, 208 and 210 sold by the company RHEOX
- BERMODOL PUR 2130 sold by the company BEROL NOBEL
- copolymers of (meth) acrylic acid and of monomers comprising at least one fatty chain are chosen from hydrophobic monomers with a fatty chain, amphiphilic monomers comprising a hydrophobic part with a fatty chain and a hydrophilic part or else mixtures thereof;
- - crosslinked copolymers of acrylic acid / C 10 -C 3 alkyl acrylate such as the products PEMULEN TR 1, PEMULEN TR 2, CARBOPOL 1382, CARBOPOL 1342 and CARBOPOL ETD 2020 sold by GOODRICH;
- - (meth) acrylic / ethyl acrylate / alkyl acrylate copolymers such as the product ACUSOL 823 sold by the company ROHM & HAAS and the product IMPERON R sold by the company HOECHST;
- Cis alkyl acrylate / polyethylene glycol acrylate (28 moles of ethylene oxide) terpolymers such as the product DAPRAL GE 202 sold by the company AK20;
- nonionic copolymers of lower alkyl (meth) acrylate (C r C 6 ) and of amphiphilic monomers comprising a fatty chain such as, for example, methyl methacrylate / stearyl acrylate polyoxyethylene copolymers such as the product ANTIL 208 sold by the company GOLDSCHMIDT;
- nonionic copolymers of hydrophilic (meth) acrylates and of hydrophobic fatty chain monomers such as, for example, polyethylene glycol methacrylate / methyl methacrylate copolymers.
- amphiphilic polymers comprising at least one fatty chain and hydrophilic units according to the invention are preferably used in an amount between 0.01 and 20% by weight of the total weight of the composition. More preferably, this amount varies from 0.1 to 15% by weight and even more preferably from 0.5 to 10% by weight.
- the cosmetically or dermatologically acceptable medium preferably consists of water or a mixture of water and cosmetically solvents acceptable such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, which can be used alone or as a mixture.
- lower alcohols such as ethanol, isopropanol
- polyalcohols such as diethylene glycol, glycol ethers, alkyl ethers of glycol or of diethylene glycol.
- the grafted silicone polymers according to the invention can be dissolved in said cosmetically acceptable medium or used in the form of an aqueous dispersion of particles.
- composition of the invention may also contain at least one additive chosen from thickeners without a fatty chain, fatty acid esters, fatty acid and glycerol esters, silicones, surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in the cosmetic field.
- at least one additive chosen from thickeners without a fatty chain, fatty acid esters, fatty acid and glycerol esters, silicones, surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in the cosmetic field.
- additives are present in the composition according to the invention in proportions which can range from 0 to 20% by weight relative to the total weight of the composition.
- the precise amount of each additive depends on its nature and is easily determined by man. art
- compositions according to the invention can be in the form of a gel, milk, cream, more or less thickened lotion or foam.
- Lotions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in foam form. Such forms of conditioning are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for fixing or treating the hair.
- compositions may also be shampoos, compositions to be rinsed or not, to be applied before or after shampooing, coloring, bleaching, perming or straightening.
- composition according to the invention when packaged in the form of an aerosol in order to obtain an aerosol lacquer or foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane , isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
- propellant can be chosen from volatile hydrocarbons such as n-butane, propane , isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures.
- Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
- the subject of the invention is also a process for the non-therapeutic treatment of keratin materials such as human hair, which consists in applying to them a composition as defined above then in optionally rinsing with water.
- the rheological properties of a conventional thickening agent of the crosslinked poly (acrylic acid) homopolymer type are studied, such as the product SYNTHALEN K sold by the company 3V in an aqueous solution containing 1% by weight of this thickener and in an aqueous solution containing 1%. by weight of this thickener and 1% by weight of grafted silicone polymer such as that described in Examples 1 and 2.
- the viscosities of the thickened solutions are measured by means of a RHEOMAT180 device equipped with the CONTRA VES TV system.
- amphiphilic polymer P comprising a fatty chain and at least one hydrophilic unit according to the invention are studied in an aqueous solution containing 1% by weight of this thickening amphiphilic polymer and in an aqueous solution containing 1% by weight. of this thickener and 1% by weight of grafted silicone polymer such as that described in Examples 1 and 2.
- index i is specific to the amphiphilic polymer studied.
- amphiphilic polymers according to the invention which have been studied are the following:
- the homopolymer poly (acrylic acid) crosslinked in combination with the silicone styling polymer of the invention decreases the viscosity of the formulation while the amphiphilic Pi polymers thickening comprising a fatty chain and at least one hydrophilic unit according to the The invention substantially increases the viscosities of the solutions containing the silicone graft polymer.
- a sensory estimation test is carried out on a panel of 5 people. The detangling and the softness to the touch are studied as cosmetic criteria after application to locks of hair, wet and sensitized of the SA 20 type. The three solutions A are applied to each of these 5 persons, on locks previously washed with shampoo. B and C below at a dose of 0.5 g per 5 g of wick:
- Solution A containing 1% by weight of the grafted silicone polymer of example 1 or 2
- Solution B containing 1% by weight of the grafted silicone polymer of Example 1 or 2 and 1% by weight of the crosslinked poly (acrylic acid) homopolymer SYNTHALEN K
- Solution C containing 1% by weight of the grafted silicone polymer of example 1 or 2 and 1% by weight of polymer P, as described above
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Abstract
A cosmetic or dermatological composition for treating keratinous material, particularly human hair, including a cosmetically or dermatologically acceptable medium containing at least one silicone-grafted polymer with a polysiloxane backbone grafted by non-silicone organic monomers and at least one amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit. Such compositions are particularly suitable for use as rinsable or non-rinsable products for washing and conditioning hair, hair setting or hair styling.
Description
COMPOSITION TOPIQUE CONTENANT UN POLYMERE SILICONE A SQUELETTETOPICAL COMPOSITION CONTAINING A SKELETED SILICONE POLYMER
POLYSILOXANE A GREFFONS NON-SILICONES ET UN POLYMEREPOLYSILOXANE WITH NON-SILICON GRAFTS AND A POLYMER
AMPHIPHILE A CHAINE GRASSEFATTY CHAIN AMPHIPHILE
La présente invention a trait à une composition cosmétique ou dermatologique pour le traitement des matières kératiniques, en particulier des cheveux humains, comprenant au moins un polymère silicone greffé, à squelette polysiloxanique greffé par des monomères organiques non-siliconés et au moins un polymère amphiphile comportant au moins une chaîne grasse et au moins un motif hydrophile.The present invention relates to a cosmetic or dermatological composition for the treatment of keratin materials, in particular human hair, comprising at least one grafted silicone polymer, with a polysiloxane skeleton grafted with non-silicone organic monomers and at least one amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit.
Les polymères du type polymère silicone greffé, à squelette polysiloxanique greffé par des monomères organiques non-siliconés sont connus dans l'art antérieur pour leurs propriétés coiffantes. Ils sont particulièrement intéressants en cosmétique capillaire du fait qu'ils apportent de la tenue aux cheveux. Leurs propriétés cosmétiques après application sur les cheveux sont néanmoins insuffisantes. On constate que les cheveux présentent après application de ces polymères, un toucher rêche et crissant résultant d'une répartition discontinue du polymère le long des fibres des cheveux.Polymers of the grafted silicone polymer type with a polysiloxane backbone grafted with non-silicone organic monomers are known in the prior art for their styling properties. They are particularly advantageous in hair cosmetics because they provide hold to the hair. Their cosmetic properties after application to the hair are nevertheless insufficient. It is found that the hair has, after application of these polymers, a rough and crunchy feel resulting from a discontinuous distribution of the polymer along the fibers of the hair.
La demanderesse a constaté que certains agents épaississants classiques, tels que, par exemple les homopolymères poly(acide acrylique) réticulés, utilisés dans des compositions capillaires contenant ces polymères particuliers, avaient tendance à diminuer la viscosité de la composition et ne permettaient pas d'améliorer sensiblement la répartition de la composition le long des fibres de cheveux mouillés ou séchés ni d'améliorer sensiblement les propriétés de douceur au toucher ou de démêlage, après application.The Applicant has found that certain conventional thickening agents, such as, for example crosslinked poly (acrylic acid) homopolymers, used in hair compositions containing these particular polymers, tended to reduce the viscosity of the composition and did not make it possible to improve substantially the distribution of the composition along the wet or dried hair fibers or significantly improve the properties of softness to the touch or disentangling, after application.
La demanderesse a trouvé de façon surprenante que l'utilisation d'un polymère amphiphile comportant au moins une chaîne grasse et au moins un motif hydrophile, comme agent épaississant dans des compositions capillaires contenant un polymère à squelette polysiloxanique greffé par des monomères organiques non-siliconés, permettait non seulement d'augmenter de façon accrue la viscosité du milieu de ces compositions mais aussi d'améliorer, à l'application, le dépôt du polymère silicone greffé le long des fibres kératiniques et d'améliorer leurs propriétés cosmétiques notamment au niveau du toucher ainsi qu'au niveau du démêlage, tout en conservant les propriétés coiffantes du polymère silicone greffé.
La composition selon l'invention est donc essentiellement caractérisée par le fait qu'elle contient dans un milieu cosmétiquement ou dermatologiquement acceptable au moins un polymère silicone greffé, à squelette polysiloxanique greffé par des monomères organiques non-siliconés et au moins un polymère amphiphile comportant au moins une chaîne grasse et au moins un motif hydrophile.The Applicant has surprisingly found that the use of an amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit, as thickening agent in hair compositions containing a polymer with a polysiloxane backbone grafted with non-silicone organic monomers , not only made it possible to increase the viscosity of the medium of these compositions in an increased manner but also to improve, on application, the deposition of the silicone polymer grafted along the keratin fibers and to improve their cosmetic properties, in particular at the level of the touch as well as at the disentangling, while retaining the styling properties of the grafted silicone polymer. The composition according to the invention is therefore essentially characterized in that it contains in a cosmetically or dermatologically acceptable medium at least one grafted silicone polymer, with a polysiloxane backbone grafted with non-silicone organic monomers and at least one amphiphilic polymer comprising at at least one fatty chain and at least one hydrophilic unit.
Dans ce qui suit, on entend désigner par polymère silicone, en conformité avec l'acceptation générale, tous polymères ou oligomères organosiliciés à structure linéaire ou cyclique, ramifiée ou réticulée, de poids moléculaire variable, obtenus par polymérisation et/ou polycondensation de silanes convenablement fonctionnalisés, et constitués pour l'essentiel par une répétition de motifs principaux dans lesquels les atomes de silicium sont reliés entre eux par des atomes d'oxygène (liaison siloxane ≡Si-O-Si≡), des radicaux hydrocarbonés éventuellement substitués étant directement liés par l'intermédiaire d'un atome de carbone sur lesdits atomes de silicium. Les radicaux hydrocarbonés les plus courants sont les radicaux alkyls notamment en Ci- C10 et en particulier méthyle, les radicaux fluoroalkyls, les radicaux aryls et en particulier phényle, et les radicaux alcényls et en particulier vinyle ; d'autres types de radicaux susceptibles d'être liés soit directement, soit par l'intermédiaire d'un radical hydrocarboné, à la chaîne siloxanique sont notamment l'hydrogène, les halogènes et en particulier le chlore, le brome ou le fluor, les thiols, les radicaux alcoxy, les radicaux poiyoxyalkylénés (ou polyéthers) et en particulier polyoxyéthylène et/ou poly- oxypropylène, les radicaux hydroxyls ou hydroxyalkyls, les groupements aminés substitués ou non, les groupements amides, les radicaux acyloxy ou acyloxyalkyls, les radicaux hydroxyalkylamino ou aminoalkyls, des groupements ammonium quaternaires, des groupements amphoteres ou bétaïniques, des groupements anioniques tels que carboxylates, thioglycolates, sulfosuccinates, thiosulfates, phosphates et sulfates, cette liste n'étant bien entendu nullement limitative (silicones dites "organomodifiées").In what follows, the term “silicone polymer” is intended to denote, in accordance with general acceptance, all organosilicon polymers or oligomers with linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and / or polycondensation of silanes suitably functionalized, and essentially consisting of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bond ≡Si-O-Si≡), optionally substituted hydrocarbon radicals being directly linked via a carbon atom on said silicon atoms. The most common hydrocarbon radicals are alkyl radicals, especially C 1 -C 10 and in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl, and alkenyl radicals and in particular vinyl; other types of radicals capable of being linked either directly or via a hydrocarbon radical to the siloxane chain are in particular hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, poiyoxyalkylenated (or polyether) radicals and in particular polyoxyethylene and / or polyoxypropylene radicals, hydroxyl or hydroxyalkyl radicals, substituted or unsubstituted amino groups, amide groups, acyloxy or acyloxyalkyl radicals, hydroxyalkylamino radicals or aminoalkyls, quaternary ammonium groups, amphoteric or betainic groups, anionic groups such as carboxylates, thioglycolates, sulfosuccinates, thiosulfates, phosphates and sulfates, this list being of course in no way limiting (so-called "organomodified" silicones).
Selon la présente invention, le ou les polymères silicones qui doivent être utilisés sont ceux qui comprennent une chaîne principale de silicone (ou polysiioxane (≡Si-0-)n) sur laquelle se trouve greffé, à l'intérieur de ladite chaîne ainsi qu'éventuellement à l'une au moins de ses extrémités, au moins un groupement organique ne comportant pas de silicone.
Ces polymères silicones peuvent être des produits commerciaux existants, ou encore être obtenus selon tout moyen connu de l'homme de l'art, en particulier par réaction entre (i) une silicone de départ correctement fonctionnalisée sur un ou plusieurs de ces atomes de silicium et (ii) un composé organique non-siliconé lui-même correctement fonctionnalisé par une fonction qui est capable de venir réagir avec le ou les groupements fonctionnels portés par ladite silicone en formant une liaison covalente ; un exemple classique d'une telle réaction est la réaction d'hydrosylilation entre des groupements ≡Si-H et des groupements vinyliques CH2=CH-, ou encore la réaction entre des groupements thio-fonctionnels -SH avec ces mêmes groupements vinyliques.According to the present invention, the silicone polymer (s) which must be used are those which comprise a main silicone chain (or polysiioxane (≡Si-0-) n ) on which is grafted, inside said chain as well as 'optionally at at least one of its ends, at least one organic group not comprising silicone. These silicone polymers can be existing commercial products, or can also be obtained by any means known to those skilled in the art, in particular by reaction between (i) a starting silicone correctly functionalized on one or more of these silicon atoms. and (ii) a non-silicone organic compound itself correctly functionalized by a function which is capable of reacting with the functional group or groups carried by said silicone by forming a covalent bond; a classic example of such a reaction is the hydrosylilation reaction between ≡Si-H groups and vinyl groups CH 2 = CH-, or the reaction between thio-functional groups -SH with these same vinyl groups.
Des exemples de polymères silicones convenant à la mise en oeuvre de la présente invention, ainsi que leur mode particulier de préparation, sont notamment décrits dans les demandes de brevets EP-A-0582152, WO93/23009 et WO 95/03776 dont les enseignements sont totalement inclus dans la présente description à titre de références non limitatives.Examples of silicone polymers suitable for the implementation of the present invention, as well as their particular mode of preparation, are described in particular in patent applications EP-A-0582152, WO93 / 23009 and WO 95/03776, the teachings of which are fully included in this description by way of non-limiting references.
Selon un mode particulièrement préféré de réalisation de la présente invention, le polymère silicone mis en oeuvre comprend le résultat de la copolymérisation radicalaire entre d'une part au moins un monomère organique anionique non-siliconé présentant une insaturation éthylénique et/ou un monomère organique hydrophobe non-siliconé présentant une insaturation éthylénique et d'autre part une silicone présentant dans sa chaîne au moins un groupement fonctionnel capable de venir réagir sur lesdites insaturations éthyléniques desdits monomères non-siliconés en formant une liaison covalente, en particulier des groupements thio-fonctionnels.According to a particularly preferred embodiment of the present invention, the silicone polymer used comprises the result of radical copolymerization between on the one hand at least one non-silicone anionic organic monomer having ethylenic unsaturation and / or one hydrophobic organic monomer non-silicone having ethylenic unsaturation and on the other hand a silicone having in its chain at least one functional group capable of reacting on said ethylenic unsaturations of said non-silicone monomers by forming a covalent bond, in particular thio-functional groups.
Selon la présente invention, lesdits monomères anioniques à insaturation éthylénique sont de préférence choisis, seuls ou en mélanges, parmi les acides carboxyliques insaturés, linéaires ou ramifiés, éventuellement partiellement ou totalement neutralisés sous la forme d'un sel, ce ou ces acides carboxyliques insaturés pouvant être plus particulièrement l'acide acrylique, l'acide méthacrylique, l'acide maléique, l'anhydride maléique, l'acide itaconique, l'acide fumarique et l'acide crotonique. Les sels convenables sont notamment les sels d'alcalins, d'alcalino-terreux et d'ammonium. On notera que, de même, dans le polymère silicone greffé final, le groupement organique à caractère anionique qui comprend le résultat de l'(homo)polymérisation radicalaire d'au moins un monomère anionique de type acide
carboxylique insaturé peut être, après réaction, post-neutralisé avec une base (soude, ammoniaque,.. ) pour l'amener sous la forme d'un selAccording to the present invention, said anionic ethylenically unsaturated monomers are preferably chosen, alone or as a mixture, from unsaturated, linear or branched carboxylic acids, optionally partially or completely neutralized in the form of a salt, this or these unsaturated carboxylic acids may more particularly be acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid. Suitable salts are especially the alkali, alkaline earth and ammonium salts. It will be noted that, likewise, in the final grafted silicone polymer, the organic group with an anionic character which comprises the result of the (homo) radical polymerization of at least one anionic monomer of acid type unsaturated carboxylic acid can be, after reaction, post-neutralized with a base (soda, ammonia, etc.) to bring it in the form of a salt
Selon la présente invention, les monomères hydrophobes à insaturation éthylénique sont de préférence choisis, seuls ou en mélanges, parmi les esters d'acide acrylique alcanols et/ou les esters d'acide méthacrylique d'alcanols. Les alcanols sont de préférence en CrCιa et plus particulièrement en CrC12 Les monomères préférentiels sont choisis dans le groupe constitué par le (méth)acrylate d'isooctyle, le (méth) acrylate d'isononyle, le 2-éthylhexyl(méth)acrylate, le (méth)acrylate de lauryle, le (méth)acrylate d'isopentyle, le (méth)acrylate de n-butyle, le (méth)acrylate d'isobutyle, le (méth)acrylate de méthyle, le (méth)acrylate de tertio-butyle, le (méth) acrylate de tπdécyle, le (méth)acrylate de stéaryle ou leurs mélangesAccording to the present invention, the hydrophobic ethylenically unsaturated monomers are preferably chosen, alone or as a mixture, from acrylic acid alkanol esters and / or methacrylic acid esters from alkanols. The alkanols are preferably in C r Cι a and more particularly in C r C 12 The preferred monomers are chosen from the group consisting of isooctyl (meth) acrylate, isononyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, isopentyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, methyl (meth) acrylate, tert-butyl (meth) acrylate, tπdecyl (meth) acrylate, stearyl (meth) acrylate or mixtures thereof
Une famille de polymères silicones greffés particulièrement bien à la mise en oeuvre de la présente invention est constituée par les polymères silicones comportant dans leur structure le motif de formule (I) suivant .A family of silicone polymers grafted particularly well to the implementation of the present invention consists of silicone polymers comprising in their structure the unit of formula (I) below.
(-S. — O-)a (-Si-O-)b ( — s. -o— )c (-S. - O-) a (-Si-O-) b (- s. -O—) c
(G2)- S- G3 G, (G2)^S -G4 ^(G 2 ) - S- G 3 G, (G 2 ) ^ S -G 4 ^
dans lequel les radicaux G1 f identiques ou différents, représentent l'hydrogène ou un radical alkyle en C1-C10 ou encore un radical phényle , les radicaux G2, identiques ou différents, représentent un groupe alkylene en Cι-C10 , G3 représente un reste poiymérique résultant de l'(homo)polyméπsatιon d'au moins un monomère anionique a insaturation éthylénique ; G4 représente un reste poiymérique résultant de l'(homo) polymérisation d'au moins un monomère hydrophobe à insaturation éthylénique ; m et n sont égaux à 0 ou 1 ; a est un nombre entier allant de 0 et 50 , b est un nombre entier pouvant être compris entre 10 et 350, c est un nombre entier allant de 0 et 50 , sous reserve que l'un des paramètres a et c soit différent de 0in which the identical or different radicals G 1 f represent hydrogen or a C 1 -C 10 alkyl radical or else a phenyl radical, the G 2 radicals, identical or different, represent a Cι-C 10 alkylene group, G 3 represents a polymer residue resulting from the (homo) polyméπsatιon of at least one anionic monomer with ethylenic unsaturation; G 4 represents a polymer residue resulting from the (homo) polymerization of at least one hydrophobic ethylenically unsaturated monomer; m and n are 0 or 1; a is an integer ranging from 0 to 50, b is an integer which can be between 10 and 350, c is an integer ranging from 0 and 50, provided that one of the parameters a and c is different from 0
De préférence, le motif de formule (I) ci-dessus présente au moins l'une, et encore plus préférentiellement l'ensemble, des caractéristiques suivantesPreferably, the motif of formula (I) above has at least one, and even more preferably all, of the following characteristics
- les radicaux G-, désignent un radical alkyle, de préférence le radical méthyle ;the radicals G- denote an alkyl radical, preferably the methyl radical;
- n est non nul, et les radicaux G2 représentent un radical divalent en C1-C3, de préférence un radical propylène ;
- G3 représente un radical poiymérique résultant de l'(homo)polyménsatιon d'au moins un monomère du type acide carboxylique à insaturation éthylénique, de préférence l'acide acrylique et/ou l'acide méthacrylique ;- n is not zero, and the radicals G 2 represent a divalent C 1 -C 3 radical, preferably a propylene radical; - G 3 represents a polymer radical resulting from the (homo) polyménsatιon of at least one monomer of the carboxylic acid type with ethylenic unsaturation, preferably acrylic acid and / or methacrylic acid;
- G4 représente un radical poiymérique résultant de l'(homo)polymérisatιon d'au moins un monomère du type (méth)acrylate d'alkyle (C1-C10), de préférence le (méth)acrylate d'isobutyle ou de méthyle.- G 4 represents a polymeric radical resulting from the (homo) polymerization of at least one monomer of the (meth) acrylate (C 1 -C 1 0) type, preferably isobutyl (meth) acrylate or methyl.
Des exemples de polymères silicones répondant à la formule (I) sont notamment des polydiméthylsiloxanes (PDMS) sur lesquels sont greffés, par l'intermédiaire d'un chaînon de raccordement de type thiopropylene, des motifs polymères mixtes du type acide poly(méth)acrylιque et du type poly(méth)acrylate de méthyle.Examples of silicone polymers corresponding to formula (I) are in particular polydimethylsiloxanes (PDMS) onto which are grafted, via a thiopropylene-type connecting link, mixed polymer units of the poly (meth) acrylic acid type. and of the poly (meth) acrylate type.
D'autres exemples de polymères silicones répondant à la formule (I) sont notamment des polydiméthylsiloxanes (PDMS) sur lesquels sont greffés, par l'intermédiaire d'un chaînon de raccordement de type thiopropylene, des motifs polymères du type poly(meth)acrylate d'isobutyleOther examples of silicone polymers corresponding to formula (I) are in particular polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting link, polymeric units of the poly (meth) acrylate type. isobutyl
De préférence, la masse moléculaire en nombre des polymères silicones de l'invention varie de 10 000 à 1 000 000 environ, et encore plus préférentiellement de 10 000 a 100 000 environPreferably, the number-average molecular mass of the silicone polymers of the invention varies from approximately 10,000 to 1,000,000, and even more preferably from approximately 10,000 to 100,000
Le polymère silicone greffé est utilisé de préférence en une quantité allant de 0,01 a 20% en poids du poids total de la composition. Plus préférentiellement, cette quantité varie de 0,1 à 15% en poids et encore plus préférentiellement de 0,5 à 10% en poidsThe grafted silicone polymer is preferably used in an amount ranging from 0.01 to 20% by weight of the total weight of the composition. More preferably, this amount varies from 0.1 to 15% by weight and even more preferably from 0.5 to 10% by weight
Les polymères amphiphiles comportant au moins une chaîne grasse et au moins un motif hydrophile, utilisés selon l'invention sont choisis de préférence dans le groupe constitué par :The amphiphilic polymers comprising at least one fatty chain and at least one hydrophilic unit, used according to the invention are preferably chosen from the group consisting of:
(1 ) les holosides modifiés par des groupements comportant au moins une chaîne grasse ,(1) holosides modified by groups comprising at least one fatty chain,
on peut citer à titre d'exemple
- les celluloses ou leurs dérivés, modifiés par des groupements comportant au moins une chaîne grasse tels que des groupes alkyls, arylalkyls, alkylaryls ou leurs mélanges où les groupes alkyls sont en C8-C22 ;we can cite as an example - celluloses or their derivatives, modified by groups comprising at least one fatty chain such as alkyl, arylalkyl, alkylaryl groups or their mixtures where the alkyl groups are C 8 -C 22 ;
- les alkylhydroxyethylcelluloses non-ioniques telles que les produits NATROSOL PLUS GRADE 330 CS et POLYSURF 67 (alkyle en C16) vendus par la société AQUALON ;- nonionic alkylhydroxyethylcelluloses such as the products NATROSOL PLUS GRADE 330 CS and POLYSURF 67 (C 16 alkyl) sold by the company AQUALON;
- les alkylhydroxyethylcelluloses quaternisées (cationiques) telles que les produits QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18-- quaternized (cationic) alkylhydroxyethylcelluloses such as the products QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18-
B (alkyle en C12) et QUATRISOFT LM-X 529-8 (alkyle en C18) vendus par la société AMERCHOL et les produits CRODACEL QM , CRODACEL QL (alkyle en Cι2) et CRODACEL QS (alkyle en Cι8) vendus par la société CRODA ;B (C 12 alkyl) and Quatrisoft LM-X 529-8 (C18 alkyl) sold by the company Amerchol, and the products Crodacel QM, Crodacel QL (C Cι 2) and Crodacel QS (C Cι 8) sold by CRODA;
- les nonoxynylhydroxyéthyicelluloses non-ioniques tels que le produit AMERCELL HM-1500 vendu par la société AMERCHOL ;- non-ionic nonoxynylhydroxyethyicelluloses such as the product AMERCELL HM-1500 sold by the company AMERCHOL;
- les alkylcelluloses non-ioniques telles que le produit BERMOCOLL EHM 100 vendu par la société BEROL NOBEL ;- non-ionic alkylcelluloses such as the product BERMOCOLL EHM 100 sold by the company BEROL NOBEL;
- les polyalcools(Cι2-C18) saccharides tels que le produit EMULSAN (mélange D- galactosamine/acide aminouronique) et le produit BIOSAN LPS-50 vendus par la société PETROFERM ;- polyalcohols (Cι 2 -C 18 ) saccharides such as the product EMULSAN (D-galactosamine / aminouronic acid mixture) and the product BIOSAN LPS-50 sold by the company PETROFERM;
- les hydroxypropylguars modifiés par une chaîne grasse tel que le produit ESAFLOR HM 22 (modifié par une chaîne alkyle en C22) vendu par la société LAMBERTI ; le produit MIRACARE XC 95-3 (modifié par une chaîne alkyle en Cι4) et le produit RE 205-146 (modifié par une chaîne alkyle en C20) vendus par RHONE-POULENC ;- hydroxypropylguars modified by a fatty chain such as the product ESAFLOR HM 22 (modified by a C 22 alkyl chain) sold by the company LAMBERTI; the product MIRACARE XC 95-3 (modified by a C 4 alkyl chain) and the product RE 205-146 (modified by a C 20 alkyl chain) sold by RHONE-POULENC;
(2) les copolymères d'anhydride maléique ou de l'un de ses dérivés et de monomères comportant au moins une chaîne grasse:(2) copolymers of maleic anhydride or one of its derivatives and of monomers comprising at least one fatty chain:
on peut citer à titre d'exemple :as an example, we can cite:
- les copolymères N-octadécylvinyléther/anhydride maléique comme le produit GANTREZ AN-8194 vendu par la société ISP ;
- les terpolymères acétate de vinyle/monomaléate d'isobutyle/néodécanoate de vinyle tels que les produits ACV-4033 et 9649-147 vendus par ISP, le produit MEYPRO- FIX 509 vendu par MEYHALL et les produits DENSODRIN BA et LIPODERM LIQUOR FP vendus par BASF;- N-octadecylvinylether / maleic anhydride copolymers such as the product GANTREZ AN-8194 sold by the company ISP; - the vinyl acetate / isobutyl monomaleate / vinyl neodecanoate terpolymers such as the products ACV-4033 and 9649-147 sold by ISP, the product MEYPRO-FIX 509 sold by MEYHALL and the products DENSODRIN BA and LIPODERM LIQUOR FP sold by BASF;
(3) les polyuréthanes et leurs dérivés comportant des groupements contenant au moins une chaîne grasse tels que par exemple les produits commerciaux suivants : RHEOLATE 205, 208 et 210 vendus par la société RHEOX ; BERMODOL PUR 2130 vendu par la société BEROL NOBEL ; ACRYSOL SCT-(3) polyurethanes and their derivatives comprising groups containing at least one fatty chain such as for example the following commercial products: RHEOLATE 205, 208 and 210 sold by the company RHEOX; BERMODOL PUR 2130 sold by the company BEROL NOBEL; ACRYSOL SCT-
275, ACRYSOL RM-870 et ACRYSOL44, DW-1206 B, DW-1206 F, DW-1206 G et DW-1206 J vendus par la société ROHM & HAAS ; DAPRAL T 212 vendu par la société AKZO275, ACRYSOL RM-870 and ACRYSOL44, DW-1206 B, DW-1206 F, DW-1206 G and DW-1206 J sold by the company ROHM &HAAS; DAPRAL T 212 sold by AKZO
(4) les copolymères de l'acide crotonique et de monomères comportant au moins une chaîne grasse ;(4) copolymers of crotonic acid and of monomers comprising at least one fatty chain;
on peut citer à titre d'exemple :as an example, we can cite:
- les terpolymères acétate de vinyle/acide crotonique/stéarate d'allyle ;- vinyl acetate / crotonic acid / allyl stearate terpolymers;
(5) les copolymères de N-vinyIpyrrolidone et de monomères comportant au moins une chaîne grasse tels que des oléfines substituées par un radical alkyle comportant une longue chaîne hydrocarbonée comme par exemple les produits ANTARON V216 et ANTARON V220 vendus par la société ISP ;(5) copolymers of N-vinyIpyrrolidone and of monomers comprising at least one fatty chain such as olefins substituted by an alkyl radical comprising a long hydrocarbon chain such as for example the products ANTARON V216 and ANTARON V220 sold by the company ISP;
(6) les copolymères d'acide (méth)acrylique et de monomères comportant au moins une chaîne grasse ; ces monomères sont choisis parmi les monomères hydrophobes à chaîne grasse, les monomères amphiphiles comportant une partie hydrophobe à chaîne grasse et une partie hydrophile ou bien leurs mélanges ;(6) copolymers of (meth) acrylic acid and of monomers comprising at least one fatty chain; these monomers are chosen from hydrophobic monomers with a fatty chain, amphiphilic monomers comprising a hydrophobic part with a fatty chain and a hydrophilic part or else mixtures thereof;
on peut citer à titre d'exemples : - les copolymères réticulés d'acide acrylique/acrylate d'alkyle en C10-C3o tels que les produits PEMULEN TR 1 , PEMULEN TR 2, CARBOPOL 1382, CARBOPOL 1342 et CARBOPOL ETD 2020 vendus par la société GOODRICH ;
- les copolymères acide (méth)acrylique/acrylate d'éthyle/acrylate d'alkyle tels que le produit ACUSOL 823 vendu par la société ROHM & HAAS et le produit IMPERON R vendu par la société HOECHST ;as examples: - crosslinked copolymers of acrylic acid / C 10 -C 3 alkyl acrylate such as the products PEMULEN TR 1, PEMULEN TR 2, CARBOPOL 1382, CARBOPOL 1342 and CARBOPOL ETD 2020 sold by GOODRICH; - (meth) acrylic / ethyl acrylate / alkyl acrylate copolymers such as the product ACUSOL 823 sold by the company ROHM & HAAS and the product IMPERON R sold by the company HOECHST;
- les copolymères réticulés acide acrylique/isodécanoate de vinyle tel que le produit STABYLEN 30 vendu par la société 3V ;- Acrylic acid / vinyl isodecanoate crosslinked copolymers such as the product STABYLEN 30 sold by the company 3V;
- les terpolymères acide acrylique/vinylpyrrolidone/méthacrylate de lauryle tels que les produits ACRYLIDONE LM, ACP-1184, ACP-1194 vendus par la société ISP ;- acrylic acid / vinylpyrrolidone / lauryl methacrylate terpolymers such as the products ACRYLIDONE LM, ACP-1184, ACP-1194 sold by the company ISP;
- les copolymères acide acrylique/(méth)acrylate de lauryle tels que les produits COATEX SX vendus par la société COATEX ;- acrylic acid / lauryl (meth) acrylate copolymers such as the COATEX SX products sold by the company COATEX;
- les terpolymères acide (méth)acrylique/acrylate d'alkyle/alkyl polyéthoxylé allyl éther tels que les produits RHEOVIS -CR, -CR3l -CR2 et -CRX vendus par la société ALLIED COLLOIDS ;- (meth) acrylic acid / alkyl acrylate / polyethoxylated alkyl allyl ether terpolymers such as the RHEOVIS -CR, -CR 3l -CR 2 and -CRX products sold by the company ALLIED COLLOIDS;
- les terpolymères acide methacrylique/acrylate d'éthyle/stéaryl polyéthoxylé allyl éther tels que les produits SALCARE-SC90 et -SC80 vendus par la société ALLIED COLLOIDS (stéaryl polyéthoxylé à 10 moles d'oxyde d'éthylène noté stéareth-10) ;- methacrylic acid / ethyl acrylate / polyethoxylated allyl ether stearyl terpolymers such as the SALCARE-SC90 and -SC80 products sold by the company ALLIED COLLOIDS (polyethoxylated stearyl with 10 moles of ethylene oxide denoted steareth-10);
- les terpolymères acide methacrylique/acrylate d'éthyle/acrylate de lauryle polyoxyéthylène tel que le produit RHEO 2000 vendu par COATEX ;- methacrylic acid / ethyl acrylate / polyoxyethylene lauryl acrylate terpolymers such as the product RHEO 2000 sold by COATEX;
- les terpolymères acide methacrylique/acrylate d'éthyle/methacrylate de stéaryle polyoxyéthylène tels que les produits ACRYSOL 22, ACRYSOL 25 et DW-1206A vendus par la société ROHM & HAAS ;- methacrylic acid / ethyl acrylate / polyoxyethylene stearyl methacrylate terpolymers such as the products ACRYSOL 22, ACRYSOL 25 and DW-1206A sold by the company ROHM &HAAS;
- les copolymères acide methacrylique/acrylate d'éthyle/acrylate de nonylphénol polyoxyéthylène tels que le produit RHEO 3000 vendu par COATEX ;- methacrylic acid / ethyl acrylate / polyoxyethylene nonylphenol acrylate copolymers such as the product RHEO 3000 sold by COATEX;
- les copolymères acide acrylique/monoitaconate de stéaryle polyoxyéthylène ou les copolymères acide acrylique/monoitaconate de cétyle polyoxyéthylène tels que les produits 8069-72A et 8069-72B vendus par NATIONAL STARCH ;
- les copolymères acide methacrylique/acrylate de butyle/monomère hydrophobe comportant au moins une chaîne grasse tels que le produit 8069-146A vendu par NATIONAL STARCH ;- the acrylic acid / polyoxyethylene stearyl monoitaconate copolymers or the acrylic acid / polyoxyethylene cetyl monoitaconate copolymers such as the products 8069-72A and 8069-72B sold by NATIONAL STARCH; - methacrylic acid / butyl acrylate / hydrophobic monomer copolymers comprising at least one fatty chain such as the product 8069-146A sold by NATIONAL STARCH;
- les terpolymères acide acrylique/acrylate d'alkyle en Cis/acrylate de polyéthylèneglycol (28 moles d'oxyde d'éthylène) tels que le produit DAPRAL GE 202 vendu par la société AK20 ;- acrylic acid / Cis alkyl acrylate / polyethylene glycol acrylate (28 moles of ethylene oxide) terpolymers such as the product DAPRAL GE 202 sold by the company AK20;
- les sels d'un ester d'acide gras partiel d'un copolymère acide acrylique/diméthyléthanolamine tels que le produit DAPRAL GE 202 DMA vendu par la société AKZO ;the salts of a partial fatty acid ester of an acrylic acid / dimethylethanolamine copolymer such as the product DAPRAL GE 202 DMA sold by the company AKZO;
- les copolymères acide acrylique/acrylate/monomère amphiphile comportant une chaîne grasse à groupements uréthane tels que le produit ADDITOL VXW 1312 vendu par HOECHST ;- acrylic acid / acrylate / amphiphilic monomer copolymers comprising a fatty chain with urethane groups such as the product ADDITOL VXW 1312 sold by HOECHST;
- les copolymères acryliques modifiés par des groupes hydrophobes à chaîne grasse tels que le produit ACUSOL 102 vendu par ROHM & HAAS ;- acrylic copolymers modified with hydrophobic groups with a fatty chain, such as the product ACUSOL 102 sold by ROHM &HAAS;
(7) les copolymères non-ioniques de (méth)acrylate d'alkyle inférieur (CrC6) et de monomères amphiphiles comportant une chaîne grasse comme par exemple les copolymères de méthacrylate de méthyle/acrylate de stéaryle polyoxyéthylène tel que le produit ANTIL 208 vendu par la société GOLDSCHMIDT ;(7) nonionic copolymers of lower alkyl (meth) acrylate (C r C 6 ) and of amphiphilic monomers comprising a fatty chain such as, for example, methyl methacrylate / stearyl acrylate polyoxyethylene copolymers such as the product ANTIL 208 sold by the company GOLDSCHMIDT;
(8) les copolymères non-ioniques de (méth)acrylates hydrophiles et de monomères hydrophobes à chaîne grasse comme par exemple les copolymères méthacrylate de poiyéthylèneglycol/méthacrylate de méthyle.(8) nonionic copolymers of hydrophilic (meth) acrylates and of hydrophobic fatty chain monomers such as, for example, polyethylene glycol methacrylate / methyl methacrylate copolymers.
Les polymères amphiphiles comportant au moins une chaîne grasse et des motifs hydrophiles selon l'invention, sont utilisés de préférence en une quantité comprise entre 0,01 et 20% en poids du poids total de la composition. Plus préférentiellement, cette quantité varie de 0,1 à 15% en poids et encore plus préférentiellement de 0,5 à 10% en poids.The amphiphilic polymers comprising at least one fatty chain and hydrophilic units according to the invention are preferably used in an amount between 0.01 and 20% by weight of the total weight of the composition. More preferably, this amount varies from 0.1 to 15% by weight and even more preferably from 0.5 to 10% by weight.
Le milieu cosmétiquement ou dermatologiquement acceptable est de préférence constitué par de l'eau ou un mélange d'eau et de solvants cosmétiquement
acceptables tels que des monoalcools, des polyalcools, des éthers de glycol ou des esters d'acides gras, qui peuvent être utilisés seuls ou en mélange.The cosmetically or dermatologically acceptable medium preferably consists of water or a mixture of water and cosmetically solvents acceptable such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, which can be used alone or as a mixture.
On peut citer plus particulièrement les alcools inférieurs tels que l'ethanol, l'isopropanol, les polyalcools tels que le diéthylèneglycol, les éthers de glycol, les alkyléthers de glycol ou de diéthylèneglycol.Mention may more particularly be made of lower alcohols such as ethanol, isopropanol, polyalcohols such as diethylene glycol, glycol ethers, alkyl ethers of glycol or of diethylene glycol.
Les polymères silicones greffés selon l'invention peuvent être dissous dans ledit mileu cosmétiquement acceptable ou utilisés sous forme de dispersion aqueuse de particules.The grafted silicone polymers according to the invention can be dissolved in said cosmetically acceptable medium or used in the form of an aqueous dispersion of particles.
La composition de l'invention peut également contenir au moins un additif choisi parmi les épaississants sans chaîne grasse, les esters d'acides gras, les esters d'acides gras et de glycérol, les silicones, les tensioactifs, les parfums, les conservateurs, les filtres solaires, les protéines, les vitamines, les polymères, les huiles végétales, animales, minérales ou synthétiques et tout autre additif classiquement utilisé dans le domaine cosmétique.The composition of the invention may also contain at least one additive chosen from thickeners without a fatty chain, fatty acid esters, fatty acid and glycerol esters, silicones, surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in the cosmetic field.
Ces additifs sont présents dans la composition selon l'invention dans des proportions pouvant aller de 0 à 20% en poids par rapport au poids total de la composition La quantité précise de chaque additif est fonction de sa nature et est déterminée facilement par l'homme de l'artThese additives are present in the composition according to the invention in proportions which can range from 0 to 20% by weight relative to the total weight of the composition. The precise amount of each additive depends on its nature and is easily determined by man. art
Bien entendu, l'homme de l'art veillera à choisir le ou les éventuels composés à ajouter à la composition selon l'invention de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition conforme à l'invention ne soient pas, ou substantiellement pas, altérées par l'addition envisagée.Of course, those skilled in the art will take care to choose the optional compound (s) to be added to the composition according to the invention in such a way that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the proposed addition.
Les compositions selon l'invention peuvent se présenter sous forme de gel, de lait, de crème, de lotion plus ou moins épaissie ou de mousse.The compositions according to the invention can be in the form of a gel, milk, cream, more or less thickened lotion or foam.
Elles sont plus particulièrement des lotions de mise en plis, des lotions pour le brushing, des compositions de fixation (laques) et de coiffage. Les lotions peuvent être conditionnées sous diverses formes notamment dans des vaporisateurs, des flacons pompes ou dans des récipients aérosols afin d'assurer une application de la composition sous forme vaporisée ou sous forme de mousse. De telles formes de
conditionnement sont indiquées, par exemple, lorsqu'on souhaite obtenir un spray, une laque ou une mousse pour la fixation ou le traitement des cheveux.They are more particularly styling lotions, brushing lotions, fixing compositions (lacquers) and styling. Lotions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in foam form. Such forms of conditioning are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for fixing or treating the hair.
Les compositions peuvent être également des shampooings, des compositions à rincer ou non, à appliquer avant ou après un shampooing, une coloration, une décoloration, une permanente ou un défrisage.The compositions may also be shampoos, compositions to be rinsed or not, to be applied before or after shampooing, coloring, bleaching, perming or straightening.
Lorsque la composition selon l'invention est conditionnée sous forme d'aérosol en vue d'obtenir une laque ou une mousse aérosol, elle comprend au moins un agent propulseur qui peut être choisi parmi les hydrocarbures volatils tels que le n-butane, le propane, l'isobutane, le pentane, un hydrocarbure chloré et/ou fluoré et leurs mélanges. On peut également utiliser en tant qu'agent propulseur le gaz carbonique, le protoxyde d'azote, le diméthyléther, l'azote, l'air comprimé et leurs mélanges.When the composition according to the invention is packaged in the form of an aerosol in order to obtain an aerosol lacquer or foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane , isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
L'invention a encore pour objet un procédé de traitement non-thérapeutique des matières kératiniques telles que les cheveux humains consistant à appliquer sur celles-ci une composition telle que définie précédemment puis à effectuer éventuellement un rinçage à l'eau.The subject of the invention is also a process for the non-therapeutic treatment of keratin materials such as human hair, which consists in applying to them a composition as defined above then in optionally rinsing with water.
L'invention va être maintenant plus complètement illustrée à l'aide des exemples suivants qui ne sauraient être considérés comme la limitant aux modes de réalisation décrits.The invention will now be more fully illustrated with the aid of the following examples which should not be considered as limiting it to the embodiments described.
EXEMPLESEXAMPLES
EXFMPl F 1 Gel de coiffageEXFMPl F 1 Styling gel
- Polymère silicone greffé de formule (I) de structure polyméthyl/méthylsiloxane à groupements propyl thio-3 acide polyméthacrylique et groupements propyl thio-3 poly(méthacrylate de méthyle) 1 g en MA- grafted silicone polymer of formula (I) of polymethyl / methylsiloxane structure with propyl thio-3 groups of polymethacrylic acid and propyl thio-3 poly groups (methyl methacrylate) 1 g in MA
- Terpolymère acide methacrylique/acrylate d'éthyle/methacrylate de stéaryle oxyéthylène (55/35/10) en dispersion aqueuse à 30%
vendu sous le nom ACRYSOL 22 par la Société ROHM & HAAS 1 g en MA- Methacrylic acid / ethyl acrylate / stearyl oxyethylene methacrylate (55/35/10) terpolymer in aqueous dispersion at 30% sold under the name ACRYSOL 22 by the company ROHM & HAAS 1 g in MA
Aminométhylpropanol neutralisation à 100% dudit polymère silicone et du terpolymère qspAminomethylpropanol 100% neutralization of said silicone polymer and of the terpolymer qs
- Eau déminéralisée qsp 100 g- Demineralized water qs 100 g
EXEMPLE 2 Gel de coiffageEXAMPLE 2 Styling gel
Polymère silicone greffé de formule (I) de structure polyméthyl/méthylsiloxane à groupements propyl thio-3 acide polyméthacrylique et groupements propyl thio-3 poly(méthacrylate de méthyle) 2 g en MAGrafted silicone polymer of formula (I) of polymethyl / methylsiloxane structure with propyl thio-3 groups polymethacrylic acid and propyl thio-3 poly (methyl methacrylate) groups 2 g in MA
Hydroxyéthylcellulose modifiée par une chaîne cétyle vendue sous le nom NATROSOL PLUS GRADE 330 S par la société AQUALON 3 g en MAHydroxyethylcellulose modified by a cetyl chain sold under the name NATROSOL PLUS GRADE 330 S by the company AQUALON 3 g in MA
Aminométhylpropanol neutralisation à 100% dudit polymère silicone greffé qspAminomethylpropanol 100% neutralization of said grafted silicone polymer qs
Eau déminéralisée qsp 100 gDemineralized water qs 100 g
ESSAIS COMPARATIFS DE VISCOSITECOMPARATIVE VISCOSITY TESTS
On étudie les propriétés rheologiques d'un agent épaississant classique du type homopolymère poly(acide acrylique) réticulé comme le produit SYNTHALEN K vendu par la société 3V dans une solution aqueuse contenant 1 % en poids de cet épaississant et dans une solution aqueuse contenant 1% en poids de cet épaississant et 1% en poids de polymère silicone greffé tel que celui décrit dans les exemples 1 et 2. On mesure les viscosités des solutions épaissies au moyen d'un appareil RHEOMAT180 équipé du système CONTRA VES TV.
On étudie les propriétés rheolologiques d'un polymère P, amphiphile comportant une chaîne grasse et au moins un motif hydrophile selon l'invention dans une solution aqueuse contenant 1% en poids de ce polymère amphiphile épaississant et dans une solution aqueuse contenant 1% en poids de cet épaississant et 1% en poids de polymère silicone greffé tel que celui décrit dans les exemples 1 et 2. Dans ce qui suit l'indice i est spécifique au polymère amphiphile étudié.The rheological properties of a conventional thickening agent of the crosslinked poly (acrylic acid) homopolymer type are studied, such as the product SYNTHALEN K sold by the company 3V in an aqueous solution containing 1% by weight of this thickener and in an aqueous solution containing 1%. by weight of this thickener and 1% by weight of grafted silicone polymer such as that described in Examples 1 and 2. The viscosities of the thickened solutions are measured by means of a RHEOMAT180 device equipped with the CONTRA VES TV system. The rheolological properties of an amphiphilic polymer P comprising a fatty chain and at least one hydrophilic unit according to the invention are studied in an aqueous solution containing 1% by weight of this thickening amphiphilic polymer and in an aqueous solution containing 1% by weight. of this thickener and 1% by weight of grafted silicone polymer such as that described in Examples 1 and 2. In what follows the index i is specific to the amphiphilic polymer studied.
Toutes les solutions sont neutralisées à pH 7,5 par de l'aminométhylpropanol.All the solutions are neutralized to pH 7.5 with aminomethylpropanol.
Les polymères amphiphiles selon l'invention qui ont été étudiés sont les suivants :The amphiphilic polymers according to the invention which have been studied are the following:
- Pi : Terpolymère acide methacrylique/acrylate d'éthyle/methacrylate de stéaryle oxyéthylène (55/35/10) en dispersion aqueuse à 30% vendu sous le nom ACRYSOL 22 par la Société ROHM & HAAS ;- Pi: methacrylic acid / ethyl acrylate / stearyl methacrylate oxyethylene (55/35/10) terpolymer in aqueous dispersion at 30% sold under the name ACRYSOL 22 by the company ROHM &HAAS;
- P2 : Terpolymère acide methacrylique/acrylate d'éthyle/stéaryl polyéthoxylé allyl éther SALCARE-SC 90 vendu par la société ALLIED COLLOIDS (stéaryl polyéthoxylé à 10 moles d'oxyde d'éthylène noté stéareth-10) ;- P 2 : Terpolymer methacrylic acid / ethyl acrylate / polyethoxylated stearyl allyl ether SALCARE-SC 90 sold by the company ALLIED COLLOIDS (polyethoxylated stearyl with 10 moles of ethylene oxide denoted steareth-10);
- P3 : Hydroxyéthylcellulose modifiée par une chaîne cétyle vendue sous le nom NATROSOL PLUS GRADE 330 S par la société AQUALON.
- P 3 : Hydroxyethylcellulose modified by a cetyl chain sold under the name NATROSOL PLUS GRADE 330 S by the company AQUALON.
On constate que l'homopolymère poly(acide acrylique) réticulé en association avec le polymère silicone de coiffage de l'invention diminue la viscosité de la formulation tandis que les polymères Pi amphiphiles épaississants comportant une chaîne grasse et au moins un motif hydrophile selon l'invention augmentent sensiblement les viscosités des solutions contenant le polymère greffé silicone.It is found that the homopolymer poly (acrylic acid) crosslinked in combination with the silicone styling polymer of the invention decreases the viscosity of the formulation while the amphiphilic Pi polymers thickening comprising a fatty chain and at least one hydrophilic unit according to the The invention substantially increases the viscosities of the solutions containing the silicone graft polymer.
ESSAIS COMPARATIFS SUR LES PROPRIETES COSMETIQUESCOMPARATIVE TESTS ON COSMETIC PROPERTIES
On effectue un test d'estimation sensorielle sur un panel de 5 personnes. On étudie comme critères cosmétiques le démêlage et la douceur au toucher après application sur des mèches de cheveux, mouillées et sensibilisées du type SA 20. On applique sur chacune de ces 5 personnes, sur des mèches préalablement lavées au shampooing, les trois solutions A, B et C suivantes à une dose de 0,5 g pour 5 g de mèche :A sensory estimation test is carried out on a panel of 5 people. The detangling and the softness to the touch are studied as cosmetic criteria after application to locks of hair, wet and sensitized of the SA 20 type. The three solutions A are applied to each of these 5 persons, on locks previously washed with shampoo. B and C below at a dose of 0.5 g per 5 g of wick:
Solution A contenant 1% en poids du polymère silicone greffé de l'exemple 1 ou 2
Solution B contenant 1% en poids du polymère silicone greffé de l'exemple 1 ou 2 et 1 % en poids de l'homopolymère poly(acide acrylique) réticulé SYNTHALEN KSolution A containing 1% by weight of the grafted silicone polymer of example 1 or 2 Solution B containing 1% by weight of the grafted silicone polymer of Example 1 or 2 and 1% by weight of the crosslinked poly (acrylic acid) homopolymer SYNTHALEN K
Solution C contenant 1 % en poids du polymère silicone greffé de l'exemple 1 ou 2 et 1% en poids de polymère P, tel que décrit ci-dessusSolution C containing 1% by weight of the grafted silicone polymer of example 1 or 2 and 1% by weight of polymer P, as described above
Toutes les solutions sont neutralisées à pH 7,5 par de l'aminométhylpropanolAll solutions are neutralized at pH 7.5 with aminomethylpropanol
Pour chaque critère cosmétique, les personnes testées attribuent une note d'appréciation de 0 à 5. Les résultats des tests sont résumes dans le tableau ci- dessousFor each cosmetic criterion, the people tested give an appreciation score of 0 to 5. The results of the tests are summarized in the table below
Les 5 personnes interrogées ont estime que la présence du polymère amphiphile épaississant a chaîne grasse et au moins un motif hydrophile selon l'invention dans la solution C contenant le polymère silicone greffé améliorait la douceur des cheveux au toucher et le démêlage des cheveux par rapport à la solution A contenant le polymère silicone greffé seul ou la solution B contenant ledit polymère silicone greffé en association avec l'épaississant classique du type homopolymère poly(acιde acrylique) réticulé
The 5 people interviewed considered that the presence of the fatty chain amphiphilic thickening polymer and at least one hydrophilic unit according to the invention in solution C containing the grafted silicone polymer improved the smoothness of the hair to the touch and the detangling of the hair compared to solution A containing the grafted silicone polymer alone or solution B containing said grafted silicone polymer in combination with the conventional thickener of the crosslinked poly (acrylic acid) homopolymer type
Claims
1. Composition cosmétique ou dermatologique destinée au traitement des matières kératiniques, caractérisée par le fait qu'elle contient dans un milieu cosmétiquement ou dermatologiquement acceptable au moins un polymère silicone greffé, à squelette polysiloxanique greffé par des monomères organiques non-siliconés et au moins au moins un polymère amphiphile comportant au moins une chaîne grasse et au moins un motif hydrophile.1. Cosmetic or dermatological composition intended for the treatment of keratinous substances, characterized in that it contains in a cosmetically or dermatologically acceptable medium at least one grafted silicone polymer, with polysiloxane skeleton grafted with non-silicone organic monomers and at least at at least one amphiphilic polymer comprising at least one fatty chain and at least one hydrophilic unit.
2. Composition selon la revendication 1 , caractérisée par le fait que le polymère silicone greffé comprend une chaîne principale de polysiloxane sur laquelle se trouve greffé, à l'intéπeur de ladite chaîne ainsi qu'éventuellement à l'une au moins de ses extrémités, au moins un groupement organique ne comportant pas de silicone2. Composition according to claim 1, characterized in that the grafted silicone polymer comprises a main chain of polysiloxane on which is grafted, inside said chain as well as possibly at at least one of its ends, at least one organic group not containing silicone
3. Composition selon la revendication 1 ou 2, caractérisée par le fait que le polymère silicone greffé est susceptible d'être obtenu par copolymérisation radicalaire entre d'une part au moins un monomère organique anionique non-siliconé présentant une insaturation éthylénique et/ou un monomère organique hydrophobe non-siliconé présentant une insaturation éthylénique et d'autre part un polysiloxane présentant dans sa chaîne au moins un, et de préférence plusieurs, groupements fonctionnels capables de venir réagir sur lesdites insaturations éthyléniques desdits monomères non-siliconés3. Composition according to claim 1 or 2, characterized in that the grafted silicone polymer is capable of being obtained by radical copolymerization between on the one hand at least one non-silicone anionic organic monomer having ethylenic unsaturation and / or one non-silicone hydrophobic organic monomer having ethylenic unsaturation and on the other hand a polysiloxane having in its chain at least one, and preferably several, functional groups capable of reacting on said ethylenic unsaturations of said non-silicone monomers
4. Composition selon la revendication 3, caracténsée par le fait que le monomères organique amonique à insaturation éthylénique est choisi, seul ou sous forme de mélange de monomères, parmi les acides carboxyliques insaturés, linéaires ou ramifiés.4. Composition according to Claim 3, characterized in that the ethylenically unsaturated amonic organic monomer is chosen, alone or in the form of a mixture of monomers, from unsaturated, linear or branched carboxylic acids.
5. Composition selon la revendication 4, caractérisée par le fait que le monomères organique amonique à insaturation éthylénique est choisi, seul ou sous forme de mélange de monomères, parmi l'acide acrylique, l'acide méthacrylique, l'acide maléique, l'anhydride maléique, l'acide itaconique, l'acide fumarique et l'acide crotonique ou leurs sels d'alcalins, d'alcalino-terreux ou d'ammonium, ou leurs mélanges. 5. Composition according to claim 4, characterized in that the organic amonic monomer containing ethylenic unsaturation is chosen, alone or in the form of a mixture of monomers, from acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid or their alkali, alkaline earth or ammonium salts, or mixtures thereof.
6 Composition selon la revendication 3, caractéπsée par le fait que le monomère organique hydrophobe à insaturation éthylénique est choisi, seul ou en mélanges de monomères, parmi les esters d'acide acrylique d'alcanol et/ou les esters d'acide méthacrylique d'alcanol, de préférence l'alcanol étant en U1-C18 6 Composition according to claim 3, caractéπsée in that the hydrophobic organic monomer with ethylenic unsaturation is chosen, alone or in mixtures of monomers, from the esters of acrylic acid of alkanol and / or the esters of methacrylic acid of alkanol, preferably the alkanol being in U 1 -C 18
7 Composition selon la revendication 6, caractérisée par le fait que le monomère organique hydrophobe à insaturation éthylénique est choisi, seul ou en mélange de monomères dans le groupe constitué par le (méth)acrylate d'isooctyle, le (méth) acrylate d'isononyle, le 2-éthylhexyl(méth)acrylate, le (méth)acrylate de lauryle, le (méth)acrylate d'isopentyle, le (méth)acrylate de n-butyle, le (méth)acrylate d'isobutyle, le (méth)acrylate de méthyle, le (méth)acrylate de tertio-butyle, le (méth) acrylate de tndécyle, le (méth)acrylate de stéaryle7 Composition according to Claim 6, characterized in that the hydrophobic organic monomer containing ethylenic unsaturation is chosen, alone or as a mixture of monomers from the group consisting of isooctyl (meth) acrylate, isononyl (meth) acrylate , 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, isopentyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, (meth) methyl acrylate, tert-butyl (meth) acrylate, tndecyl (meth) acrylate, stearyl (meth) acrylate
8 Composition selon l'une quelconque des revendications 1 a 7, caractérisée par le fait que le polymère silicone greffé comprend sur la chaîne silicone pnncipale, au moins un groupement organique à caractère anionique obtenu par r(homo)polymeπsatιon radicalaire d'au moins un monomère anionique de type acide carboxylique msature, partiellement ou totalement neutralisé sous la forme d'un sel8 Composition according to any one of claims 1 to 7, characterized in that the grafted silicone polymer comprises on the pnncipale silicone chain, at least one organic group with anionic character obtained by r (homo) radical polymeπsatιon of at least one anionic monomer of the msature carboxylic acid type, partially or totally neutralized in the form of a salt
9 Composition selon l'une quelconque des revendications 1 à 8, caractérisée par le fait que le polymère silicone greffé est choisi parmi les polymères silicones comportant dans leur structure le motif de formule (I) suivant9 Composition according to any one of claims 1 to 8, characterized in that the grafted silicone polymer is chosen from silicone polymers comprising in their structure the unit of formula (I) according to
(- ?Si' — O-). ( — ? S.'-0-)b (- ?S1<-0 — )c (-? If '- O-). (-? S .'- 0-) b (-? S1 < -0 -) c
(G2)-S-G3 G, (G2)^S-G4 (|) dans lequel les radicaux d , identiques ou différents, représentent l'hydrogène ou un radical alkyle en C1-C10 ou encore un radical phényle , les radicaux G2 , identiques ou différents, représentent un groupe alkylene en CrC10 , G3 représente un reste poiymérique résultant de r(homo)polymérιsatιon d'au moins un monomère amonique a insaturation éthylénique , G4 représente un reste poiymérique résultant de l'(homo)polymérιsatιon d'au moins un monomère hydrophobe à insaturation éthylénique ; m et n sont égaux à 0 ou 1 ; a est un nombre entier allant de 0 et 50 ; b est un nombre entier pouvant être compris entre 10 et 350, c est un nombre entier allant de 0 et 50 ; sous réserve que l'un des paramètres a et c soit différent de 0 (G 2 ) -SG 3 G, (G 2 ) ^ SG 4 (|) in which the radicals d, which are identical or different, represent hydrogen or a C 1 -C 1 alkyl radical or a phenyl radical, the radicals G 2 , identical or different, represent a C r C 10 alkylene group, G 3 represents a polymer residue resulting from r (homo) polymerization of at least one ethylenically unsaturated amonic monomer, G 4 represents a resulting polymer residue (homo) polymer of at least one hydrophobic ethylenically unsaturated monomer; m and n are 0 or 1; a is an integer ranging from 0 and 50; b is an integer which can be between 10 and 350, c is an integer ranging from 0 to 50; provided that one of the parameters a and c is different from 0
10. Composition selon la revendication 9, caractérisée par le fait que le motif de formule (I) présente au moins l'une des caractéristiques suivantes :10. Composition according to claim 9, characterized in that the unit of formula (I) has at least one of the following characteristics:
- les radicaux d désignent un radical alkyle en C1-C10 ',the radicals d denote a C1-C1 0 ' alkyl radical,
- n est non nul, et les radicaux G2 représentent un radical divalent en C1-C3 ;- n is not zero, and the radicals G 2 represent a divalent C 1 -C 3 radical;
- G3 représente un radical poiymérique résultant de r(homo)polymérisation d'au moins un monomère du type acide carboxylique à insaturation éthylénique ;- G 3 represents a polymeric radical resulting from r (homo) polymerization of at least one monomer of the carboxylic acid type with ethylenic unsaturation;
- G4 représente un radical poiymérique résultant de l'(homo)polymérisation d'au moins un monomère du type (méth)acrylate d'alkyle(Cι-Cιo).- G 4 represents a polymeric radical resulting from the (homo) polymerization of at least one monomer of the (meth) acrylate (Cι-Cιo) type.
11. Composition selon la revendication 9 ou 10, caractérisée par le fait que le motif de formule (I) présente simultanément les caractéristiques suivantes :11. Composition according to claim 9 or 10, characterized in that the unit of formula (I) simultaneously has the following characteristics:
- les radicaux G1 désignent un radical méthyle ; - n est non nul, et les radicaux G2 représentent un radical propylène ;- The radicals G 1 denote a methyl radical; - n is not zero, and the radicals G 2 represent a propylene radical;
- G3 représente un radical poiymérique résultant de r(homo)polymérisation d'au moins l'acide acrylique et/ou l'acide méthacrylique ;- G 3 represents a polymeric radical resulting from r (homo) polymerization of at least acrylic acid and / or methacrylic acid;
- G4 représente un radical poiymérique résultant de r(homo)polymérisation d'au moins un monomère du type (méth)acrylate d'isobutyle ou de méthyle.- G 4 represents a polymeric radical resulting from r (homo) polymerization of at least one monomer of the (meth) acrylate or isobutyl or methyl type.
12. Composition selon l'une quelconque des revendications 1 à 11 , caractérisée par le fait que la masse moléculaire en nombre du polymère silicone greffé varie de 10 000 à 1 000 000 environ, et encore plus préférentiellement de 10 000 à 100 000 environ.12. Composition according to any one of claims 1 to 11, characterized in that the number-average molecular mass of the grafted silicone polymer varies from 10,000 to 1,000,000 approximately, and even more preferably from 10,000 to 100,000 approximately.
13. Composition selon l'une quelconque des revendications 1 à 12, caractérisée par le fait que le polymère silicone greffé est utilisé en une quantité allant de 0,01 à 20% en poids par rapport au poids total de la composition et de préférence de 0,1 à 15% en poids et préférentiellement, cette quantité varie de 0,1 à 15% en poids et encore plus préférentiellement de 0,5 à 10% en poids.13. Composition according to any one of claims 1 to 12, characterized in that the grafted silicone polymer is used in an amount ranging from 0.01 to 20% by weight relative to the total weight of the composition and preferably 0.1 to 15% by weight and preferably, this amount varies from 0.1 to 15% by weight and even more preferably from 0.5 to 10% by weight.
14. Composition selon l'une quelconque des revendications 1 à 13, caractérisée par le fait que les polymères amphiphiles comportant au moins une chaîne grasse et des motifs hydrophiles sont choisis dans le groupe constitué par :14. Composition according to any one of claims 1 to 13, characterized in that the amphiphilic polymers comprising at least one fatty chain and hydrophilic units are chosen from the group consisting of:
(1) les holosides modifiés par des groupes comportant au moins une chaîne grasse (2) les copolymères d'anhydride maléique ou de l'un de ses dérivés et de monomères comportant au moins une chaîne grasse:(1) holosides modified by groups comprising at least one fatty chain (2) copolymers of maleic anhydride or one of its derivatives and of monomers comprising at least one fatty chain:
(3) les polyurethanes et leurs dérivés comportant des groupements comportant au moins une chaîne grasse ;(3) polyurethanes and their derivatives comprising groups comprising at least one fatty chain;
(4) les copolymères de l'acide crotonique et de monomères comportant au moins une chaîne grasse ;(4) copolymers of crotonic acid and of monomers comprising at least one fatty chain;
(5) les copolymères de N-vinylpyrrolidone et de monomères comportant au moins une chaîne grasse ;(5) copolymers of N-vinylpyrrolidone and of monomers comprising at least one fatty chain;
(6) les copolymères d'acide (méth)acrylique et de monomères comportant au moins une chaîne grasse ; ces monomères étant choisis dans le groupe constitué par les monomères hydrophobes à chaîne grasse, les monomères amphiphiles comportant une partie hydrophobe à chaîne grasse et une partie hydrophile ou bien leurs mélanges ;(6) copolymers of (meth) acrylic acid and of monomers comprising at least one fatty chain; these monomers being chosen from the group consisting of hydrophobic fatty chain monomers, amphiphilic monomers comprising a hydrophobic fatty chain part and a hydrophilic part or their mixtures;
(7) les copolymères non-ioniques de (méth)acrylate d'alkyle inférieur (Cι-C6) et de monomères amphiphiles comportant une chaîne grasse ;(7) nonionic copolymers of (lower meth) acrylate (Cι-C 6 ) and of amphiphilic monomers comprising a fatty chain;
(8) les copolymères non-ioniques de (méth)acrylates hydrophiles et de monomères hydrophobes à chaîne grasse.(8) nonionic copolymers of hydrophilic (meth) acrylates and hydrophobic fatty chain monomers.
15. Composition selon l'une quelconque des revendications 1 à 14, caractérisée par le fait que les polymères amphiphiles comportant au moins une chaîne grasse et au moins un motif hydrophile sont utilisés en une quantité allant de 0,01 à 10% en poids du poids total de la composition et plus préférentiellement de 0,5 à 10% en poids.15. Composition according to any one of claims 1 to 14, characterized in that the amphiphilic polymers comprising at least one fatty chain and at least one hydrophilic unit are used in an amount ranging from 0.01 to 10% by weight of the total weight of the composition and more preferably from 0.5 to 10% by weight.
16. Composition selon l'une quelconque des revendications 1 à 15, caractérisée par le fait qu'elle contient en plus au moins un additif choisi dans le groupe constitué par les épaississants sans chaîne grasse, les esters d'acides gras, les esters d'acides gras et de glycérol, les silicones, les tensioactifs, les parfums, les conservateurs, les filtres solaires, les protéines, les vitamines, les polymères, les huiles végétales, animales, minérales ou synthétiques et tout autre additif classiquement utilisé dans le domaine cosmétique16. Composition according to any one of claims 1 to 15, characterized in that it additionally contains at least one additive chosen from the group consisting of thickeners without fatty chain, fatty acid esters, esters of fatty acids and glycerol, silicones, surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable oils, animal, mineral or synthetic and any other additive conventionally used in the cosmetic field
17 Composition selon l'une quelconque des revendications 1 a 16, caractérisée par le fait que le milieu cosmétiquement ou dermatologiquement acceptable est constitue par de l'eau ou un mélange d'eau et d'au moins un solvant cosmétiquement acceptable17 Composition according to any one of claims 1 to 16, characterized in that the cosmetically or dermatologically acceptable medium is constituted by water or a mixture of water and at least one cosmetically acceptable solvent
18 Composition selon la revendication 17, caractérisée par le fait que les solvants cosmétiquement acceptables sont choisis dans le groupe constitue par les monoalcools, les polyalcools, les éthers de glycol, les esters d'acides gras et leurs mélanges18 Composition according to Claim 17, characterized in that the cosmetically acceptable solvents are chosen from the group consisting of monoalcohols, polyalcohols, glycol ethers, fatty acid esters and their mixtures
19 Composition selon l'une quelconque des revendications 1 a 18, caractéπsée par le fait que le polymère silicone greffé est dissous dans le milieu cosmétiquement ou dermatologiquement acceptable ou utilisé sous forme de dispersion aqueuse de particules19 Composition according to any one of claims 1 to 18, characterized in that the grafted silicone polymer is dissolved in the cosmetically or dermatologically acceptable medium or used in the form of an aqueous dispersion of particles
20 Composition selon l'une quelconque des revendications 1 a 19, caractérisée par le fait que les matières kératiniques sont des cheveux humains20 Composition according to any one of claims 1 to 19, characterized in that the keratin materials are human hair
21 Composition selon l'une quelconque des revendications 1 a 20, caractérisée par le fait qu'elle se présente sous forme de gel, de lait, de crème, de lotion plus ou moins épaissie ou de mousse21 Composition according to any one of claims 1 to 20, characterized in that it is in the form of gel, milk, cream, more or less thickened lotion or foam
22 Composition selon l'une quelconque des revendications 1 à 20, caractérisée par le fait qu'elle est un produit de coiffage22 Composition according to any one of claims 1 to 20, characterized in that it is a styling product
23 Composition selon l'une quelconque des revendications 1 à 22, caractéπsée par le fait qu'elle est un produit capillaire choisi dans le groupe constitué par des shampooings , des produits capillaires a rincer ou non, a appliquer avant ou après un shampooing, une coloration, une décoloration, une permanente ou un défrisage23 Composition according to any one of claims 1 to 22, characterized by the fact that it is a hair product chosen from the group consisting of shampoos, hair products to rinse or not, to be applied before or after shampooing, a coloring, discoloration, perm or straightening
24 Composition selon l'une quelconque des revendications 1 à 23, caractéπsée par le fait qu'elle est conditionnée sous forme de vapoπsateur, de flacon pompe ou bien dans un récipient aérosol en vue d'obtenir un spray, une laque ou une mousse 25. Procédé non-thérapeutique de traitement des matières kératiniques, en particulier des cheveux humains, caractérisé par le fait qu'il consiste à appliquer sur lesdites matières une composition telle que définie selon l'une quelconque des revendications 1 à 24 puis à effectuer éventuellement un rinçage à l'eau. 24 Composition according to any one of claims 1 to 23, characterized by the fact that it is packaged in the form of a vaporizer, a pump bottle or else in an aerosol container in order to obtain a spray, a lacquer or a foam 25. Non-therapeutic method for treating keratin materials, in particular human hair, characterized in that it consists in applying to said materials a composition as defined according to any one of claims 1 to 24 then in optionally effecting rinse with water.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/981,561 US6132707A (en) | 1995-09-29 | 1996-09-16 | Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer |
| EP96931854A EP0854699B1 (en) | 1995-09-29 | 1996-09-16 | Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer |
| JP9514008A JPH10510555A (en) | 1995-09-29 | 1996-09-16 | Topical composition comprising a silicone polymer having a polysiloxane skeleton containing a non-silicone graft and a fatty chain amphiphilic polymer |
| DE69633017T DE69633017T2 (en) | 1995-09-29 | 1996-09-16 | Composition for topical application, which contains a silicone polymer with polysiloxane backbone and non-allconic grafts and an amphiphilic polymer with fatty chain |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR95/11482 | 1995-09-29 | ||
| FR9511482A FR2739282B1 (en) | 1995-09-29 | 1995-09-29 | TOPICAL COMPOSITION CONTAINING A POLYSILOXANE SKELETON POLYMER WITH NON-SILICON GRAFTS AND AN AMPHIPHILIC FATTY CHAIN POLYMER |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/589,515 Continuation US6630136B1 (en) | 1995-09-29 | 2000-06-08 | Topical composition containing a silicone polymer with a polysiloxane skeleton containing non-silicone grafts and a fatty-chain amphiphilic polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997012586A1 true WO1997012586A1 (en) | 1997-04-10 |
Family
ID=9483073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1996/001436 WO1997012586A1 (en) | 1995-09-29 | 1996-09-16 | Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6132707A (en) |
| EP (1) | EP0854699B1 (en) |
| JP (1) | JPH10510555A (en) |
| DE (1) | DE69633017T2 (en) |
| FR (1) | FR2739282B1 (en) |
| WO (1) | WO1997012586A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6932964B1 (en) | 1998-08-26 | 2005-08-23 | Basf Aktiengesellschaft | Cosmetic composition with water-soluble or water-dispersible polymers |
| US7128412B2 (en) | 2003-10-03 | 2006-10-31 | Xerox Corporation | Printing processes employing intermediate transfer with molten intermediate transfer materials |
| EP3387217A4 (en) * | 2015-12-08 | 2019-07-31 | Kemira Oyj | Liquid polymer compositions |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2751533B1 (en) * | 1996-07-23 | 2003-08-15 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS CONTAINING A NON-IONIC AMPHIPHILIC POLYMER |
| FR2758334B1 (en) * | 1997-01-14 | 1999-05-21 | Oreal | THICK AQUEOUS COMPOSITION COMPRISING AN AMPHIPHILIC POLYMER AND A POLYOXYALKYLENE SILICONE AND USE IN COSMETICS |
| FR2773477B1 (en) * | 1998-01-13 | 2001-02-23 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
| FR2773474B1 (en) * | 1998-01-13 | 2002-10-11 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
| FR2782636B1 (en) * | 1998-08-27 | 2001-09-14 | Oreal | COMPOSITIONS CONTAINING A POLYCONDENSATE COMPRISING AT LEAST ONE POLYURETHANE AND / OR POLYUREA PATTERN AND A SILICONE COMPRISING AT LEAST ONE CARBOXYL FUNCTION |
| FR2788976B1 (en) * | 1999-01-29 | 2003-05-30 | Oreal | KERATIN FIBER DECOLORING ANHYDROUS COMPOSITION COMPRISING THE ASSOCIATION OF A WATER-SOLUBLE THICKENING POLYMER AND A NON-IONIC AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE FAT CHAIN |
| FR2799956B1 (en) * | 1999-10-20 | 2001-12-07 | Oreal | COSMETIC COMPOSITIONS CONTAINING A VINTLDIMETHICONE / DIMETHICONE COPOLYMER IN AQUEOUS EMULSION AND A THICKENER THEREOF AND USES THEREOF |
| US6514918B1 (en) | 2000-08-18 | 2003-02-04 | Johnson & Johnson Consumer Companies, Inc. | Viscous, mild, and effective cleansing compositions |
| FR2818534B1 (en) * | 2000-12-22 | 2003-09-26 | Oreal | AEROSOL DEVICE CONTAINING A POLYURETHANE AND / OR POLYURIDE AND A BINDING POLYMER |
| US7959198B2 (en) * | 2002-05-16 | 2011-06-14 | Labor Saving Systems, Ltd. | Magnetic line retrieval system and method |
| US20050074260A1 (en) * | 2003-10-03 | 2005-04-07 | Xerox Corporation | Printing apparatus and processes employing intermediate transfer with molten intermediate transfer materials |
| FR2874823B1 (en) * | 2004-09-09 | 2007-04-13 | Oreal | AEROSOL DEVICE CONTAINING AT LEAST ONE ACRYLIC ASSOCIATIVE POLYMER AND AT LEAST ONE FIXING POLYMER |
| US20060078507A1 (en) * | 2004-09-09 | 2006-04-13 | Charles Gringore | Aerosol device containing a composition comprising at least one propellant, at least one acrylic associative polymer, and at least one fixative polymer |
| GB0624132D0 (en) * | 2006-12-02 | 2007-01-10 | Unilever Plc | Hair conditioning compositions |
| US11179312B2 (en) * | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
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| WO1991015186A1 (en) * | 1990-04-06 | 1991-10-17 | The Procter & Gamble Company | Hair styling conditioners |
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- 1996-09-16 DE DE69633017T patent/DE69633017T2/en not_active Expired - Fee Related
- 1996-09-16 EP EP96931854A patent/EP0854699B1/en not_active Expired - Lifetime
- 1996-09-16 WO PCT/FR1996/001436 patent/WO1997012586A1/en active IP Right Grant
- 1996-09-16 US US08/981,561 patent/US6132707A/en not_active Expired - Fee Related
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| EP0412705A2 (en) * | 1989-08-07 | 1991-02-13 | The Procter & Gamble Company | Vehicle systems for use in cosmetic compositions |
| WO1991015186A1 (en) * | 1990-04-06 | 1991-10-17 | The Procter & Gamble Company | Hair styling conditioners |
| WO1992016179A2 (en) * | 1991-03-19 | 1992-10-01 | The Procter & Gamble Company | Hair care compositions having styling/conditioning agent and plasticizer |
| EP0524612A2 (en) * | 1991-07-22 | 1993-01-27 | Kao Corporation | Modified silicone containing hair cosmetic |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6932964B1 (en) | 1998-08-26 | 2005-08-23 | Basf Aktiengesellschaft | Cosmetic composition with water-soluble or water-dispersible polymers |
| US7128412B2 (en) | 2003-10-03 | 2006-10-31 | Xerox Corporation | Printing processes employing intermediate transfer with molten intermediate transfer materials |
| US7241853B2 (en) | 2003-10-03 | 2007-07-10 | Xerox Corporation | Printing processes employing intermediate transfer with molten intermediate transfer materials |
| EP3387217A4 (en) * | 2015-12-08 | 2019-07-31 | Kemira Oyj | Liquid polymer compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0854699A1 (en) | 1998-07-29 |
| FR2739282B1 (en) | 1997-10-31 |
| DE69633017D1 (en) | 2004-09-02 |
| FR2739282A1 (en) | 1997-04-04 |
| JPH10510555A (en) | 1998-10-13 |
| US6630136B1 (en) | 2003-10-07 |
| DE69633017T2 (en) | 2005-07-21 |
| EP0854699B1 (en) | 2004-07-28 |
| US6132707A (en) | 2000-10-17 |
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